Acetic Anhydride → HCID 18770477, compound

HRID 2275507Notes

Reaction equation

HRID 2275507 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([NH2:16])[C:6]3[C:11]([N:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>C(O)(=O)C>[C:17]([NH:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([NH2:16])[C:6]3[C:11]([N:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1)(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 31624Acridine, 2,9-diamino-

Product 1

HCID 18770477HCID 18770477, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a 5 mL rbf equipped with condenser and a nitrogen bubbler were charged 2,9-diaminoacridine (100 mg, 0.48 mmol) and acetic acid (300 μL). To the resulting solution was added acetic anhydride (47 μL, 0.50 mmol). The reaction mixture was heated to reflux for 10 min under a nitrogen atmosphere. LCMS showed only formation of expected product and some traces of starting material. The reaction mixture was concentrated to dryness. NMR showed desired product, alkanes impurities coming from starting material sample and acetic acid left. The residue was dissolved in water and washed with DCM to remove the alkanes impurities. The aqueous layer was lyophilised to afford 2-acetamidyl-9-aminoacridine as a brown solid (130 mg, quantitative). Analyses by 1H NMR and LCMS conformed to structure.

Workup

  1. customTo a 5 mL rbf equipped with condenser
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 10 min under a nitrogen atmosphere

Sources & evidence

ORD record
ord-612841149d2e44dba03efceb469d1d7e
Source dataset
uspto-grants-2015_09
Patent number
US09127164B2

Reaction notes

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